The Messy Middle

The Messy Middle • Scott Belsky

⭑ 7.5 Stars

Few books hit home for me as much as The Messy Middle did. Scott Belsky tackled one of the most important, yet often unspoken truths about starting a company - it sucks. While I generally believe that we’ve moved past romanticizing the process of building a startup that became so prevalent around the release of Aaron Sorkin’s The Social Network, very little is ever mentioned about the valley that’s endured between the launch of a new company, and either their successful exit or more likely their death.

The rapturous headlines that praise big funding rounds and even bigger acquisitions only perpetuate the belief that all startups scale rapidly, and that the majority of them succeed - as Biz Stone puts it, the 10-year overnight success. Unfortunately, most startups don’t succeed, the majority of them fail and do so in agonizing fashion for the team onboard the ship.

In this book, Belsky uses his own experience founding, building, and eventually exiting Behance, to explain to the reader just how tedious and agonizing the process is for founding teams. As a founder currently navigating the messy middle of a journey myself, this book had my attention from beginning to end, and produced a regular wave of emotions throughout the process.